Ammonia → HCID 58868549, compound

HRID 400337Notes

Reaction equation

HRID 400337 reaction equation
[NH3:1].[O:2]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][CH:16]3[O:18][CH2:17]3)[CH:11]=2)[CH:6]=[CH:5][C:3]1=[O:4]>C(O)C>[NH2:1][CH2:17][CH:16]([OH:18])[CH2:15][CH2:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][C:3](=[O:4])[O:2]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58868555HCID 58868555, compound

Product 1

HCID 58868549HCID 58868549, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

5 ml of 30% aqueous ammonia and Gd (OTf3) (0.039 g, 0.065 mmol) are added to a solution of racemic 4-(7-coumarinyloxy)-1,2-epoxybutane (0.150 g, 0.65 mmol) in 2 ml of ethanol. It is heated at 65° C. for 15 hours, the solvent is evaporated, the residue is diluted in ethyl acetate, and it is washed with an NaCl-saturated solution. The residue provides the crude amine (0.081 g, yield 50%) that is used without purification for the next stage.

Workup

  1. customthe solvent is evaporated
  2. additionthe residue is diluted in ethyl acetate
  3. washit is washed with an NaCl-saturated solution

Sources & evidence

ORD record
ord-1ee5c601f41b440988e9b2344cb109b8
Source dataset
uspto-grants-2014_06
Patent number
US08741593B2

Reaction notes

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